The personal blog of Adam Nash

Blogging

“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something – your gut, destiny, life, karma, whatever. Because believing that the dots will connect down the road will give you the confidence to follow your heart even when it leads you off the well worn path; and that will make all the difference.”

I’ve always loved startups and venture capital, and I had been fortunate enough after leaving LinkedIn to have a chance to work for Greylock Partners, one of the most successful firms in the industry.

In May of 2012, my daughter was born. While on parental leave, I remember receiving a note about a Greylock company that was looking to add to its executive team. I had visited that company just the month before, to help advise on strategies for organizing and executing on viral growth.

The role itself wasn’t the right fit, but for some reason that company stuck in my head. Did I really want to become a full time investor? Or did I want to go help build a company?

As it turns out, the company that I couldn’t get out of my head was Dropbox.

First moments after the birth of my daughter, May 2012.

Opportunity at Scale

Over my career, I’ve had the good fortune to work at three companies that grew to reach over 100 million users. After spending the past six years focused on building new companies, I’m excited about jumping back into the challenges of designing and shipping features for the more than 500 million people who use Dropbox to get things done.

With the proliferation of devices and ubiquitous connectivity of the modern workplace, I think there is a unique opportunity, right now, to help teams unleash their creative energy and find more enlightened ways of working together.

Drew has done a great job of sharing the high level vision for Dropbox, and I’m excited to dive into a space that has so much product potential. The era of walled gardens is over, and there has been an explosion of new applications and content types in the past few years. The challenge is to design an open ecosystem that helps bring all of those capabilities together in a way that doesn’t sacrifice simplicity in design.

Connecting the Dots

For now, I just want to say thank you John Lilly for reconnecting me to the Dropbox team, and thank you to Quentin, Drew, and the entire Dropbox team for this opportunity. It is truly amazing how life connects the dots.

Over the past few years, there haven’t been many posts on my personal blog. Most of my writing time was dedicated to pieces for Wealthfront, although some of the drop off is likely do to the 140-character competition from Twitter.

Despite the drop off, I’ve been reviewing my blog posts from 2013 & 2014, and they seem to stand up quite well.

Diving into a startup is all encompassing, but over the past few months quite a few people have asked me questions about the Executive in Residence (EIR) role. Some of these people have had offers to become EIRs, others are curious about the role and whether they should pursue it as a career option. For most, however, it’s just genuine curiosity the EIR role is largely a low volume, undocumented role that is very unique to the private equity & venture capital ecosystems.

One of the guide posts for this blog has been a dedicated effort to take the questions that I receive regularly, and translate them into thoughtful and useful content to be broadly shared. So before my experiences of 2012 fade into the shrouds of history, I’ve decided to write a quick series about my experience as an EIR, and the most common questions I’ve received.

Tomorrow is my first day at Wealthfront, and I couldn’t be more excited.

As many long time readers know, personal finance has always been a passion of mine. However, now that I’m moving from this being a personal passion to a professional role, there are some important disclosures that have to be made.

First, it needs to be stated that Psychohistory is my personalblog and is not written in my capacity as COO of Wealthfront Inc. Nothing on this blog should be construed as, nor is it intended to be, personal investment advice. The content of this blog represents my own views and/or opinions and does not represent the views and/or opinions of Wealthfront Inc.

Second, I’ve added a Disclosure tab to this blog, to ensure that at any time, any new visitor will have quick access to this information.

Third, none of the historical content of this blog is being modified from its original. Those articles were written for purely personal reasons, and are appropriate for the time they were published. That being said, going forward, I’m only going to publish content related to personal finance and investing through the official Wealthfront blog. Wealthfront has published a fantastic series of articles on a wide range of topics, and I feel privileged to be added as one of the contributing authors there.

The WordPress.com stats helper monkeys prepared a 2012 annual report for this blog.

Here’s an excerpt:

About 55,000 tourists visit Liechtenstein every year. This blog was viewed about 310,000 times in 2012. If it were Liechtenstein, it would take about 6 years for that many people to see it. Your blog had more visits than a small country in Europe!

In February 2012, I wrote a blog post that indicted the Dow Jones Industrial Average for including Cisco in 2009 instead of Apple. At the time, Apple had just crossed $500 per share, and that simple decision had cost the US the psychology of an index hitting new highs.

I was driving home on Sunday, listening to the radio, and it occurred to me how different the financial news would be if Apple ($AAPL) was in the Dow Jones Industrial Average (^DJI).

Of course, being who I am, I went home and built a spreadsheet to recalculate what would have happened if Dow Jones had decided to add Apple to the index instead of Cisco back in 2009. Imagine my surprise to see that the Dow be over 2000 points higher.

Update: AAPL at $700

With the launch of the iPhone 5, we find ourselves roughly 7 months later. For fun, I re-ran the spreadsheet that calculated what the DJIA would be at if they had added AAPL to the index in 2009 instead of CSCO. (To date, I’ve never seen an explanation on why Cisco was selected to represent computer hardware instead of Apple.)

Result: Dow 16,600

As of September 17, 2012, AAPL closed at 699.781/share. As it turns out, if Dow Jones had added Apple instead of Cisco in 2009, the index would now be at 16,617.82. Hard to think that hitting all new highs wouldn’t be material for market psychology and the election.

For those of you who read this blog regularly, you’ve likely noticed a lull in my posting. That’s because, about two weeks ago, my wife & I welcomed a new addition to the family. Given that the most common response to our decision to add a fourth child to the family has largely been “borderline insanity”, I felt it was appropriate to share some of my thinking on the complexity that comes with every new addition.

The Wrong Model: Linear

When a couple decides to have a second child, you are quickly inundated with advice on how to manage the complexity. The most common refrain you hear is: “Don’t worry, you can still field man-on-man coverage.” Another popular version of this advice is: “At least you’re not outnumbered.”

The implication here is that managing the family is fundamentally a relationship between parents & kids, like this:

Parental Ratio = # of Parents / # of Kids

With the implication that somehow, as long as the parental ratio is greater than or equal to one, you’ll be able to manage.

Unfortunately, I’ve found that this description of complexity dramatically understates the drama of real family life.

The Right Model: Combinatorics

Instead 0f focusing specifically on the number and types of nodes in the family graph, I think it’s more useful to think about the nature of emotional entanglements (aka “drama”) and understand that they tend to require at least two people, but can easily involve more. As a result, the complexity of family life can be more accurately modeled as the number of two-party relationships in a family that can engage in drama.

Initially, a couple has exactly one potential pair:

Adult 1 <-> Adult 2

However, once you add a single child to the mix, you immediately add two more vectors of potential drama:

Adult 1 <-> Child 1

Adult 2 <-> Child 1

It’s worth noting that it’s sometimes unclear whether a three-party argument is truly a single argument or actually a combination of two or three two-party arguments, but let’s just roll with the simplified assumption for now that all drama can be decomposed to pair-based drama.

Pascal’s Triangle actually makes calculating this number for any size family trivial. This means that:

Two family members (0 kids): 1 drama pair

Three family members (1 kids): 3 drama pairs

Four family members (2 kids): 6 drama pairs

Five family members (3 kids): 10 drama pairs

Six family members (4 kids): 15 drama pairs

It’s combinatoric, specifically in the form of:

family complexity = # of family members choose 2

Which is a fancy way of saying each new child adds a new relationship to the mix for every existing family member. This sequence is also known as the triangular numbers.

For those of you who have or come from large families, let me know if this lightweight graph theory matches your experience.